Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
twitter

MetaCyc Compound: IMP

Synonyms: 5'-IMP, ribosylhypoxanthine monophosphate, inosinate, inosine monophosphate, inosine 5'-monophosphate, inosine 5'-phosphate, 5'-inosinate, 5'-inosinic acid, 5'-inosine monophosphate

Superclasses: a nucleic acid component a nucleotide a nucleoside 5'-monophosphate a ribonucleoside 5'-monophosphate a purine ribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a purine nucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a ribonucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a ribonucleotide a ribonucleoside 5'-monophosphate a purine ribonucleoside 5'-monophosphate
a nucleic acid component
an organic heterocyclic compound an organic heterobicyclic compound a purine a purine nucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a purine a purine nucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate

Chemical Formula: C10H11N4O8P

Molecular Weight: 346.19 Daltons

Monoisotopic Molecular Weight: 348.04709992489995 Daltons

IMP compound structure

SMILES: C(OP(=O)([O-])[O-])C1(OC(C(O)C(O)1)N3(C=NC2(C(=O)NC=NC=23)))

InChI: InChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/p-2/t4-,6-,7-,10-/m1/s1

InChIKey: InChIKey=GRSZFWQUAKGDAV-KQYNXXCUSA-L

Unification Links: CAS:131-99-7 , ChEBI:58053 , ChemSpider:5482599 , HMDB:HMDB00175 , IAF1260:33960 , KEGG:C00130 , MetaboLights:MTBLC58053 , PubChem:7140378

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -244.30493 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

adenosine nucleotides degradation I :
IMP + H2O → inosine + phosphate

adenosine ribonucleotides de novo biosynthesis :
L-aspartate + IMP + GTP → adenylo-succinate + GDP + phosphate + 2 H+

Not in pathways:
IMP + H2O → hypoxanthine + D-ribofuranose 5-phosphate

Not in pathways:
a ribonucleoside 5'-monophosphate + H2O → a ribonucleoside + phosphate

Not in pathways:
ribonucleotiden + ribonucleotiden + ATP → ribonucleotidem+n + AMP + diphosphate

Not in pathways:
a nucleoside 5'-monophosphate[periplasmic space] + H2O[periplasmic space] → a nucleoside[periplasmic space] + phosphate[periplasmic space]
a nucleoside 5'-monophosphate + ATP → a nucleoside diphosphate + ADP

Not in pathways:
a nucleotide + H2O → a nucleoside + phosphate

Reactions known to produce the compound:

adenine and adenosine salvage V :
inosine + ATP → IMP + ADP + H+

adenosine nucleotides degradation I :
AMP + H+ + H2O → IMP + ammonium

Not in pathways:
IDP + H2O → IMP + phosphate + H+
ITP + H2O → IMP + diphosphate + H+
ammonium + IMP + NADP+ ← GMP + NADPH + 2 H+

tRNA processing :
a tRNA precursor with a 5' extension and a long 3' trailer + H2O → a tRNA precursor with a 5' extension + a ribonucleoside 5'-monophosphate
a tRNA precursor with a 5' extension and a short 3' extension → a tRNA precursor with a 5' extension + a ribonucleoside 5'-monophosphate

Not in pathways:
a single stranded DNA + H2O → a ribonucleoside 5'-monophosphate + a single-stranded oligodeoxyribonucleotide
a single-stranded RNA + n H2O → n a ribonucleoside 5'-monophosphate

Not in pathways:
a tRNA precursor + H2O → a tRNA + a ribonucleotide

tRNA processing :
a tRNA precursor with a 5' extension and a long 3' trailer + n H2O → a tRNA precursor with a 5' extension and a short 3' extension + n a nucleoside 5'-monophosphate
a tRNA precursor with a short 3' extension → an uncharged tRNA + n a nucleoside 5'-monophosphate

Not in pathways:
a nucleoside 3',5'-bisphosphate + H2O → a nucleoside 5'-monophosphate + phosphate
a nucleoside triphosphate + 2 H2O → a nucleoside 5'-monophosphate + 2 phosphate + 2 H+
a tRNA precursor + H2O → a tRNA + a nucleoside 5'-monophosphate
RNase II degradation substrate mRNA + n H2O → n a nucleoside 5'-monophosphate
mutated tRNA + n H2O → n a nucleoside 5'-monophosphate
DNAn + n H2O → n a nucleoside 5'-monophosphate
RNA + n H2O → n a nucleoside 5'-monophosphate
a double stranded DNA + H2O → a double stranded DNA + a nucleoside 5'-monophosphate
(deoxynucleotides)(n) + H2O → (deoxynucleotides)(n-1) + a nucleoside 5'-monophosphate
a RNA-DNA hybrid + n H2O → DNA + n a nucleoside 5'-monophosphate
a 2-O-methylated RNA + n H2O → n a nucleoside 5'-monophosphate
RNase R degradation substrate RNA + n-1 H2O → n-2 a nucleoside 5'-monophosphate + a diribonucleotide
an oligonucleotide + H2O → n a nucleoside 5'-monophosphate

Reactions known to both consume and produce the compound:

adenine and adenosine salvage III , adenine and adenosine salvage IV :
IMP + diphosphate ↔ hypoxanthine + 5-phospho-α-D-ribose 1-diphosphate

adenosine nucleotides degradation I , guanosine ribonucleotides de novo biosynthesis , urate biosynthesis/inosine 5'-phosphate degradation :
IMP + NAD+ + H2O ↔ XMP + NADH + H+

inosine-5'-phosphate biosynthesis I , inosine-5'-phosphate biosynthesis II , inosine-5'-phosphate biosynthesis III :
IMP + H2O ↔ 5-formamido-1-(5-phospho-D-ribosyl)-imidazole-4-carboxamide

In Reactions of unknown directionality:

Not in pathways:
a purine ribonucleoside + diphosphate = a purine ribonucleoside 5'-monophosphate + phosphate + H+

Not in pathways:
a nucleoside 5'-monophosphate + ATP = a 5'-phosphonucleoside 3'-diphosphate + AMP + H+
a lipopolysaccharide + a nucleoside diphosphocholine = a phosphorylcholine-6-O-hexose-lipopolysaccharide + a nucleoside 5'-monophosphate + H+
a dinucleotide (nucleic acid) + H2O = 2 a nucleoside 5'-monophosphate + 2 H+
a nucleoside diphosphate + H2O = a nucleoside 5'-monophosphate + phosphate + H+
a p-nitrophenyl 5'-nucleotide + H2O = a nucleoside 5'-monophosphate + 4-nitrophenol + 2 H+

Not in pathways:
a nucleotide + a 2'-deoxynucleoside = a nucleoside + a 2'-deoxyribonucleoside 5'-monophosphate

In Transport reactions:
IMP[cytosol]IMP[periplasmic space]

Enzymes activated by IMP, sorted by the type of activation, are:

Activator (Allosteric) of: carbamoyl phosphate synthetase [Anderson77, Trotta74]

Enzymes inhibited by IMP, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: phosphoribosylaminoimidazole-succinocarboxamide synthase [Nelson05]

Inhibitor (Mechanism unknown) of: amidophosphoribosyl transferase [Messenger79] , methylenetetrahydrofolate dehydrogenase [Dev78] , hypoxanthine phosphoribosyltransferase [Hochstadt78a, Guddat02] , xanthine phosphoribosyltransferase [Liu83, Comment 1] , guanylate kinase [Oeschger66] , glycogen phosphorylase [Dombradi85]

This compound has been characterized as an alternative substrate of the following enzymes: alkaline phosphatase , farnesyl diphosphate phosphatase , guanylate kinase , AMP 5'-nucleotidase


References

Anderson77: Anderson PM (1977). "Binding of allosteric effectors to carbamyl-phosphate synthetase from Escherichia coli." Biochemistry 1977;16(4);587-93. PMID: 189806

Dev78: Dev IK, Harvey RJ (1978). "A complex of N5,N10-methylenetetrahydrofolate dehydrogenase and N5,N10-methenyltetrahydrofolate cyclohydrolase in Escherichia coli. Purification, subunit structure, and allosteric inhibition by N10-formyltetrahydrofolate." J Biol Chem 1978;253(12);4245-53. PMID: 350870

Dombradi85: Dombradi V, Hajdu J, Friedrich P, Bot G (1985). "Purification and characterization of glycogen phosphorylase from Drosophila melanogaster." Insect Biochem. Vol. 15, No. 3, pp. 403-410.

Guddat02: Guddat LW, Vos S, Martin JL, Keough DT, de Jersey J (2002). "Crystal structures of free, IMP-, and GMP-bound Escherichia coli hypoxanthine phosphoribosyltransferase." Protein Sci 11(7);1626-38. PMID: 12070315

Hochstadt78a: Hochstadt J (1978). "Hypoxanthine phosphoribosyltransferase and guanine phosphoribosyltransferase from enteric bacteria." Methods Enzymol 1978;51;549-58. PMID: 692401

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Liu83: Liu SW, Milman G (1983). "Purification and characterization of Escherichia coli guanine-xanthine phosphoribosyltransferase produced by a high efficiency expression plasmid utilizing a lambda PL promoter and CI857 temperature-sensitive repressor." J Biol Chem 1983;258(12);7469-75. PMID: 6305942

Messenger79: Messenger LJ, Zalkin H (1979). "Glutamine phosphoribosylpyrophosphate amidotransferase from Escherichia coli. Purification and properties." J Biol Chem 1979;254(9);3382-92. PMID: 372191

Nelson05: Nelson SW, Binkowski DJ, Honzatko RB, Fromm HJ (2005). "Mechanism of action of Escherichia coli phosphoribosylaminoimidazolesuccinocarboxamide synthetase." Biochemistry 44(2);766-74. PMID: 15641804

Oeschger66: Oeschger MP, Bessman MJ (1966). "Purification and properties of guanylate kinase from Escherichia coli." J Biol Chem 1966;241(22);5452-60. PMID: 5333666

Trotta74: Trotta PP, Pinkus LM, Haschemeyer RH, Meister A (1974). "Reversible dissociation of the monomer of glutamine-dependent carbamyl phosphate synthetase into catalytically active heavy and light subunits." J Biol Chem 1974;249(2);492-9. PMID: 4358555


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Thu Aug 27, 2015, BIOCYC14B.